He shouldn't have a problem fitting things like the sunglass case, even with the gussets if he stuffs the bag for a while and sends it to the spa. This bag is able to stand on its own in more rigid leathers and it is actually pretty roomy compared to some other bags in similar sizes (38 cm/14-15 inches). But his bag is starting to have the same issues as that burgundy epsom bag available at collector square. The leather softened with time and the structure of the bag has collapsed a bit, maybe it has been squeezed in storage or something.
The color combo is really beautiful, is it the same as
Filippo Fiora's kelly a depeche?
I really wish they would make this bag agian, or maybe an updated version.